US4764526A - Azolylvinyl ethers and pesticidal use - Google Patents

Azolylvinyl ethers and pesticidal use Download PDF

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US4764526A
US4764526A US07/027,105 US2710587A US4764526A US 4764526 A US4764526 A US 4764526A US 2710587 A US2710587 A US 2710587A US 4764526 A US4764526 A US 4764526A
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sub
carbon atoms
dimethyl
butene
compound
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Klaus Bockmann
Gerhard Jager
Wilhelm Brandes
Gerd Hanssler
Paul Reinecke
Wilhelm Stendel
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to new azolylvinyl ethers, a process for their preparation and their use as fungicides and as ectoparasiticidal agents.
  • disulphides such as, for example, zinc ethylene-1,2-bisdithiocarbamidate
  • disulphides are good agents for combating fungal plant diseases (compare R. Wegler, “Chemie der convinced für Schweizer- und Schadlingsbekampfungsstoff” ("Chemistry of plant protection agents and agents for combating pests"), Volume 2, page 59 et seq., Springer Verlag 1970).
  • R 1 represents alkyl, alkenyl, alkinyl, alkoxyalkyl, optionally substituted phenyl, optionally substituted phenylalkyl, optionally substituted phenoxyalkyl, optionally substituted phenoxyalkoxyalkyl, naphthoxyalkyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl,
  • R 2 represents alkyl, halogenoalkyl, optionally substituted cycloalkyl or the grouping R 3 --C(CH 3 ) 2 --, or also represents optionally substituted phenyl, if R 1 represents optionally substituted phenoxyalkyl or optionally substituted phenoxyalkoxyalkyl and A represents a nitrogen atom, and
  • R 3 represents in each case optionally substituted phenyl, phenoxy or phenoxyalkyl
  • the compounds of the formula (I) can exist in two geometric isomer forms, depending on the arrangement of the groups bonded to the double bond; they are preferentially obtained in a varying isomer ratio.
  • the present invention relates both to the individual isomers and to the isomer mixtures.
  • R 1 has the abovementioned meaning
  • Z represents an electron-attracting leaving grouping
  • the new azolylvinyl ethers of the formula (I) have powerful fungicidal properties and are also suitable for combating ectoparasites in the field of animal husbandry and animal breeding.
  • the compounds according to the invention exhibit better funigicidal actions than the compounds 2-(4-chlorophenoxy)-4,4-dimethyl-1-(imidazol-1-yl)- and (1,2,4-triazol-1-yl)-1-penten-3-one and zinc ethylene 1,2-bisdithiocarbamidate, which are known from the prior art.
  • the active compounds according to the invention thus represent an enrichment of the art.
  • Formula (I) provides a general definition of the azolylvinyl ethers according to the invention.
  • this formula preferably,
  • A represents a nitrogen atom or the CH group
  • R 1 represents straight-chain or branched alkyl with 1 to 12 carbon atoms, alkenyl or alkinyl with in each case 2 to 20 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in each alkyl part or naphthoxyalkyl with 1 to 4 carbon atoms in the alkyl part, or represents phenyl, phenylalkyl with 1 to 4 carbon atoms in the alkyl part, phenoxyalkyl with 1 to 4 carbon atoms in the alkyl part and phenoxyalkoxyalkyl with 1 to 4 carbon atoms in each alkyl part, each of which is optionally monosubstituted or polysubstituted by identical or different substituents in the phenyl part, substituents on the phenyl which may be mentioned in each case being: halogen, alkyl and alkoxy with in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy and halogen
  • R 1 furthermore preferably represents cycloalkyl or cycloalkylalkyl with in each case 5 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part and in each case optionally monosubstituted or polysubstituted by identical or different alkyl radicals with 1 to 4 carbon atoms;
  • R 2 represents straight-chain or branched alkyl with 1 to 8 carbon atoms, halogeno-tert,-butyl with 1 or 2 halogen atoms or the grouping R 3 --C(CH 3 ) 2 --, or represents cycloalkyl which has 5 to 7 carbon atoms and is optionally monosubstituted or polysubstituted by identical or different alkyl radicals with 1 to 4 carbon atoms; or furthermore also represents phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents, possible substituents being the substituents on phenyl already mentioned for R 1 , if R 1 represents optionally substituted phenoxyalkyl or optionally substituted phenoxyalkoxyalkyl and A represents a nitrogen atom; and
  • R 3 represents phenyl, phenoxy or phenoxyalkyl with 1 to 4 carbon atoms in the alkyl part, in each case optionally monosubstituted or polysubstituted by identical or different substituents in the phenyl part.
  • Particularly preferred compounds of the formula (I) are those in which
  • A represents a nitrogen atom or the CH group
  • R 1 represents straight-chain or branched alkyl with 1 to 8 carbon atoms, or represents alkenyl with 2 to 18 carbon atoms or alkinyl with 2 to 6 carbon atoms, or represents alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 or 2 carbon atoms in the alkyl part, or represents naphthoxyalkyl with 1 or 2 carbon atoms in the alkyl part; or, furthermore, represents phenyl, phenylalkyl with 1 or 2 carbon atoms in the alkyl part, phenoxyalkyl with 1 or 2 carbon atoms in the alkyl part or phenoxyalkoxyalkyl with 1 or 2 carbon atoms in each alkyl part, in each case optionally mono-, di- or tri-substituted by identical or different substituents in the phenyl part, substituents on the phenyl which may be mentioned in each case being: fluorine, chlorine, bromine, straight-chain or
  • R 2 represents straight-chain or branched alkyl with 1 to 6 carbon atoms, or represents fluorotert.-butyl, chloro-tert.-butyl, 1,1-bis-(fluoromethyl)-ethyl, 1,1-bis-(chloromethyl)-ethyl or the grouping R 3 --C(CH 3 ) 2 --, or represents cyclopentyl or cyclohexyl, in each case optionally mono- or di-substituted by identical or different substituents from the group comprising methyl, ethyl and isopropyl; or furthermore also represents phenyl which is optionally mono-, di- or tri-substituted by identical or different substituents, possible substituents being the substituents on phenyl already mentioned for R 1 , if R 1 represents optionally substituted phenoxyalkyl or optionally substituted phenoxyalkoxyalkyl and A represents a nitrogen atom; and
  • R 3 represents phenyl, phenoxy or phenoxyalkyl with 1 or 2 carbon atoms in the alkyl part, in each case optionally mono-, di- or tri-substituted by identical or different substituents in the phenyl part, possible substituents being the substituents on phenyl already mentioned for R 1 .
  • Preferred compounds according to the invention are also the addition products of acids and those azolylvinyl ethers of the formula (I) in which the substituents A, R 1 and R 2 have the meanings which have already been mentioned as preferred for these substituents.
  • Preferred acids which can be added on include hydrogen halide acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, and furthermore phosphoric acid, nitric acid, monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, and sulphonic acids, such as p-toluenesulphonic acid and 1,5-naphthalenedisulphonic acid.
  • hydrogen halide acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid
  • phosphoric acid phosphoric acid
  • nitric acid monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids
  • acetic acid such as, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred here.
  • Possible anions of these salts are those which are derived from those acids which lead to physiologically acceptable addition products.
  • particularly preferred acids of this type are the hydrogen halide acids, such as, for example, hydrochloric acid and hydrobromic acid, and nitric acid and sulphuric acid.
  • Formula (II) provides a general definition of the azolylmethyl ketones to be used as starting substances in carrying out the process according to the invention.
  • a and R 2 preferably represent the radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the azolylmethyl ketones of the formula (II) are known (in this context, compare, for example, DE-OS (German Published Specification) No. 2,431,407, DE-OS (German Published Specification) No. 2,610,022, DE-OS (German Published Specification) No. 2,638,470, U.S. application Ser. No. 438,086, filed Nov. 1, 1982, now pending, and U.S. Pat. No.
  • Formula (III) provides a general definition of the compounds also to be used as starting substances for the process according to the invention.
  • R 1 preferably represents those radicals which have already been mentioned as preferred for this substituent in connection with the description of the substances of the formula (I) according to the invention.
  • Z preferably represents an electron-attracting leaving grouping, such as, for example, halogen, p-methylphenylsulphonyloxy, the grouping --O--SO 2 --OR or --NR 3 -- and the like, R here representing, for example, alkyl with 1 to 4 carbon atoms.
  • the compounds of the formula (III) are generally known compounds of organic chemistry.
  • Possible diluents for the process according to the invention are aprotic, polar solvents. These include, preferably, dimethylformamide, dimethylacetamide, dimethylsulphoxide, N-methylpyrrolidine, 2 -pyrrolidinone and hexamethylphosphoric acid triamide. In some cases, it may be advantageous to mix these solvents with other customary inert organic solvents, such as, for example, aromatic hydrocarbons.
  • the process according to the invention is carried out in the presence of a strong base.
  • a strong base such as, preferably, alkali metal hydrides, hydroxides or carbonates, for example sodium hydride and sodium hydroxide; and tertiary amines, such as triethylamine, piperidine and pyridine.
  • reaction temperatures can be varied within a substantial range in carrying out the process according to the invention.
  • the reaction is carried out between 0° C. and 120° C., preferably between 20° C. and 100° C.
  • the process according to the invention can also be carried out in a two-phase system, such as, for example, aqueous sodium hydroxide solution or potassium hydroxide solution, toluene or methylene chloride, if appropriate with the addition of 0.1 to 1 mole of a phase transfer catalyst, such as, for example, ammonium or phosphonium compounds, examples which may be mentioned being benzyldodecyl-dimethylammonium chloride and triethyl-benzyl-ammonium chloride.
  • a phase transfer catalyst such as, for example, ammonium or phosphonium compounds, examples which may be mentioned being benzyldodecyl-dimethylammonium chloride and triethyl-benzyl-ammonium chloride.
  • the acid addition salts of the compounds of the formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving the compound of the formula (I) in a suitable inert solvent and adding the acid, e.g. hydrochloric acid, and can be purified, if appropriate, by washing with an organic solvent.
  • a suitable inert solvent for example by dissolving the compound of the formula (I) in a suitable inert solvent and adding the acid, e.g. hydrochloric acid, and can be purified, if appropriate, by washing with an organic solvent.
  • the metal salt complexes of compounds of the formula (I) can be obtained in a simple manner by customary processes, thus, for example, by dissolving the metal salt in alcohol, for example ethanol, and adding the solution to compounds of the formula (I).
  • the metal salt complexes can be purified in a known manner, for example by filtration.
  • the active compounds according to the invention exhibit a powerful microbicidal action and can be employed in practice for combating undesired micro-oranisms.
  • the active compounds are suitable for use as plant protection agents.
  • Fungicidal agents in plant protection are employed for combating Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • the good toleration, by plants, of the active compounds, at the concentrations required for combating plant diseases permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with particularly good success for combating Venturia species, such as against the apple scab causative organism (Venturia inaequalis); rice diseases, such as Pyricularia oryzae and Pellicularia sasakii; and cereal diseases, such as cereal mildew, Cochliobolus sativus, Drechslera graminea, Leptosphaeria nodorum and Pyrenophora teres.
  • Venturia species such as against the apple scab causative organism (Venturia inaequalis)
  • rice diseases such as Pyricularia oryzae and Pellicularia sasakii
  • cereal diseases such as cereal mildew, Cochliobolus sativus, Drechslera graminea, Leptosphaeria nodorum and Pyrenophora teres.
  • Botrytis species such as, for example, Botrytis cinerea
  • Plasmopara species such as, for example, Plasmopara viticola
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Venturia species such as, for example, Venturia inaequalis
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Phytophthora species such as, for example, Phytophthora infestans
  • Erysiphe species such as, for example, Erysiphe graminis
  • Puccinia species such as, for example, Puccinia recondita
  • Fusarium species such as, for example, Fusarium species, such as, for example, Fusarium
  • Helminthosporium Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form Drechslera, Syn. Helminthosporium), Cercosporia species, such as, for example, Cercospora canescens.
  • the substances according to the invention not only have a protective action but in some cases are also systemic. Thus, it is possible to protect plants from fungal attack if the active compounds are fed to the above-ground parts of the plant via the soil and the root or via the seed.
  • the substances according to the invention When used in appropriate amounts, the substances according to the invention also exhibit growth-regulating properties.
  • the active compounds according to the invention are also suitable for combating ectoparasites in the field of animal husbandry and animal breeding, it being possible to achieve better results by combating the pets, for example higher milk outputs, heavier weight, more attractive animal coat, longer life and the like.
  • the active compounds according to the invention are used in the known manner, such as by external application in the form, for example, of dipping, spraying, pouring on and spotting on and dusting, or by oral administration, for example via the feed or drinking water, in the form of, for example, tablets, capsules, drinks and granules.
  • the active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, seed treatment powders, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
  • customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, seed treatment powders, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges
  • formulations are produced in known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
  • extenders that is, liquid solvents, liquefied gases under pressure, and/or solid carriers
  • surface-active agents that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents there are suitable in the main: aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water; by liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers
  • Adhesive such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs and azo-metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and Prussian Blue
  • organic dyestuffs such as alizarin dyestuffs and azo-metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the formulation or in the various use forms as a mixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellents, growth factors, plant nutrients and agents for improving soil structure.
  • active compounds such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellents, growth factors, plant nutrients and agents for improving soil structure.
  • the active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the customary manner, for example by watering, immersion, spraying, atomizing, misting, vaporizing, injecting, forming a slurry, brushing on, dusting, scattering, dry dressing, moist dressing, wet dressing, slurry dressing or encrusting.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
  • active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the place of action.
  • the active compound content of the use forms prepared from the commercially available formulations can be varied within wide limits.
  • the active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • a solution of 1678 (1 mol) 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone in 400 ml of dry dimethylformamide is added dropwise to a mixture of 30 g of sodium hydride (80% strength) and 100 ml of dry dimethylformamide at room temperature.
  • the mixture is stirred at 35° C. until the solution is clear, and a solution of 330 g of 2-(4-chlorophenoxy)-ethyl 4-methylphenylsulphonate in 500 ml of dry dimethylformamide is then added dropwise at room temperature.
  • the reaction mixture is stirred at 40° C. for 12 hours and poured onto 3 liters of water. It is extracted three times with 750 ml of ethyl acetate each time and the combined organic phases are washed three times with 500 ml of water each time, dried over sodium sulphate and concentrated in vacuo. The residue is distilled.
  • Emulsifier 0.3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 20° C. and a relative atmospheric humidity of about 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • Emulsifier 0.3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier, to the desired concentration.
  • Evaluation of the disease infestation is carried out 4 days after the inoculation.
  • Emulsifier 0.3 parts by weight of alkylarly polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier, to the desired concentration.
  • standard soil in which young rice plants have been grown is watered with 40 ml of the preparation of active compound. 7 days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. Thereafter, the plants remain in a greenhouse at a temperature of 25° C. and a relative atmospheric humidity of 100% until they are evaluated.
  • Evaluation of the disease infestation is carried out 4 days after the inoculation.
  • Emulsifier 0.25 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%.
  • Evaluation is carried out 7 days after the inoculation.
  • Drechslera graminea test barley
  • seed treatment seed treatment (syn. Helminthosporium gramineum)
  • the active compounds are used as dry dressings. These are prepared by extending the particular active compound with a ground mineral to give a finely pulverulent mixture, which ensures uniform distribution on the seed surface.
  • the infected seed is shaken with the dressing in a closed glass flask for 3 minutes.
  • the seed is embedded in sieved, moist standard soil and is exposed to a temperature of 4° C. in closed Petri dishes in a refrigerator for 10 days. Germination of the barley, and possibly also of the fungus spores, is thereby initiated. 2 batches of 50 grains of the pregerminated barley are subsequently sown 3 cm deep in standard soil and are cultivated in a greenhouse at a temperature of about 18° C., in seedboxes which are exposed to light for 15 hours daily.
  • Test subject All the development stages of Psoroptes ovis removed as skin scrapings from artificially infected cattle 1 hour before the start of the test.
  • Test method Transfer of 10-25 mites/concentration to 1 ml of the active compound concentratio to be tested. Subsequent transfer to and storage in a climatically controlled test room (28° C.+1° C., 80% relative humidity ⁇ 10%). Check on the action after 24 hours with a stereomicroscope, 12.5-fold magnification).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US07/027,105 1984-05-11 1987-03-13 Azolylvinyl ethers and pesticidal use Expired - Fee Related US4764526A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843417468 DE3417468A1 (de) 1984-05-11 1984-05-11 Azolylvinylether
DE3417468 1984-05-11

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US06727962 Continuation 1985-04-26

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US6054588A (en) * 1997-08-14 2000-04-25 Hoffman-La Roche Inc. Heterocyclic vinyl ethers

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DE3700916A1 (de) * 1987-01-14 1988-07-28 Bayer Ag Halogenalkyl-, alkenyl- und alkinyl-azole
US4783474A (en) * 1985-07-20 1988-11-08 Bayer Aktiengesellschaft Halogenoalkyl-, alkenyl- and alkinyl-azoles

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DE2638470A1 (de) * 1975-08-26 1977-03-31 Ici Ltd Imidazole und 1,2,4-triazole, verfahren zur herstellung derselben, solche verbindungen enthaltende zusammensetzungen zur bekaempfung von schaedlingen und verfahren zur bekaempfung von schaedlingen
DE2757113A1 (de) * 1977-12-21 1979-06-28 Siegfried Ag Imidazolylvinylaether und verfahren zu ihrer herstellung
DE2839388A1 (de) * 1978-09-11 1980-03-27 Siegfried Ag Imidazolylvinylaether und deren verwendung
US4291044A (en) * 1978-10-28 1981-09-22 Bayer Aktiengesellschaft Combating fungi with 1-(azol-1-yl)-2-substituted-alken-3-ones
WO1982002552A1 (en) * 1981-01-23 1982-08-05 Zirngibl Ludwig Method for the preparation of imidazolyl-vinyl-ethers
EP0079856A1 (de) * 1981-11-12 1983-05-25 Ciba-Geigy Ag Mikrobizide Triazolyl-vinyläther
DE3313499A1 (de) * 1983-04-14 1984-10-18 Hoechst Ag, 6230 Frankfurt 1,2,4-triazol-1-yl-vinylether, ihre herstellung und ihre verwendung als pflanzenbehandlungsmittel
EP0149235A1 (de) * 1984-01-19 1985-07-24 CELAMERCK GmbH & Co. KG Neuartige Azole mit Enoletherstruktur, ihre Herstellung und Verwendung
EP0170831A1 (de) * 1984-06-19 1986-02-12 BASF Aktiengesellschaft Azolylether, Verfahren zur Herstellung und ihre Verwendung als Fungizide

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DE2638470A1 (de) * 1975-08-26 1977-03-31 Ici Ltd Imidazole und 1,2,4-triazole, verfahren zur herstellung derselben, solche verbindungen enthaltende zusammensetzungen zur bekaempfung von schaedlingen und verfahren zur bekaempfung von schaedlingen
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EP0079856A1 (de) * 1981-11-12 1983-05-25 Ciba-Geigy Ag Mikrobizide Triazolyl-vinyläther
DE3313499A1 (de) * 1983-04-14 1984-10-18 Hoechst Ag, 6230 Frankfurt 1,2,4-triazol-1-yl-vinylether, ihre herstellung und ihre verwendung als pflanzenbehandlungsmittel
EP0149235A1 (de) * 1984-01-19 1985-07-24 CELAMERCK GmbH & Co. KG Neuartige Azole mit Enoletherstruktur, ihre Herstellung und Verwendung
EP0170831A1 (de) * 1984-06-19 1986-02-12 BASF Aktiengesellschaft Azolylether, Verfahren zur Herstellung und ihre Verwendung als Fungizide

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
US6054588A (en) * 1997-08-14 2000-04-25 Hoffman-La Roche Inc. Heterocyclic vinyl ethers
US6248901B1 (en) 1997-08-14 2001-06-19 Hoffman-La Roche Inc. Heterocyclic vinyl ethers

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BR8502226A (pt) 1986-01-14
DK207585A (da) 1985-11-12
DK207585D0 (da) 1985-05-10
DE3417468A1 (de) 1985-11-14
DD235173A5 (de) 1986-04-30
ZA853550B (en) 1985-12-24
GR851124B (enrdf_load_stackoverflow) 1985-11-25
EP0160931A2 (de) 1985-11-13
HUT38214A (en) 1986-05-28
JPS60260560A (ja) 1985-12-23
KR850008164A (ko) 1985-12-13
IL75128A0 (en) 1985-09-29
ES543036A0 (es) 1986-01-01
AU4223685A (en) 1985-11-14
NZ212011A (en) 1989-02-24
EP0160931A3 (de) 1986-12-17

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